Ashlee Simpson: Fun Fearless Female of the Year

She has an album that rocks, a megahit reality show, and a dishy love life. And now Ashlee's being honored with Cosmo's top title! Listen in as she talks about high-profile life.

Oct 25, 2005

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The defining moment Ashlee Simpson slipped out of her famous sister's shadow: When her debut album, Autobiography, hit number one on the music charts last July 28. Now the 20-year-old is a star in her own right with an album whose hardedged pop tunes are so addictive that it should come with a warning stamp and a megahit reality show heading into its second season. Although Ashlee showed talent from an early age (at 11, she was accepted into the prestigious School of American Ballet's summer course), her dreams of a performing career were put on hold at age 14, when she and her parents, Joe and Tina, left Dallas to move to L.A. and go on tour with Jessica. Ashlee became a backup dancer for Jessica, but she wasn't content in the background. Her big break came in 2002, when she landed the role of Cecilia on 7th Heaven. But singing is her primary passion, so her dad (who is now her manager as well as Jessica's) took Ashlee around to record labels. She was signed by Geffen Records in 2003—and the rest is history. Despite being a new recording artist, Ashlee bravely stood up to music executives who wanted her to make a sweeter pop album—like her sister's. More evidence of her gutsiness: She made that record and went through her first heartbreak on her reality-TV show, The Ashlee Simpson Show. But it was the aftermath of last October's Saturday Night Live lipsynching fiasco that really tested her.

While she admitted it was a mortifying experience, she handled it with grace. "It was a blip in her career, and it's incredible how she's bounced back. Most people would have curled up in a ball, but she faced it head-on," says Geffen Records rep Jim Merlis. Jessica defended Ashlee's talent by saying "She's already sold three million records, which is more than I sold in two years."

According to Ashlee, the support she's received has enabled her to move on. "All I can do is continue to work hard and do my best at the thing I love. It's cool how the fans have been supportive. I have a wonderful family and friends who love me, and that's what's most important." Read on to find out more reasons why we picked her to be our Fun Fearless Female 2005.

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Cosmo: Is your album, Autobiography, as personal as the title indicates?

Ashlee: It's about what I was going through at that point in my life— having my heart broken for the first time. I wanted to be honest and not worry about what people thought.

C: Your song "Shadow" makes it sound like you had a sad childhood. Is that accurate?

A: It wasn't that I had a sad childhood, but when I was around 14, I hadn't grown into my face yet and was all awkward and ugly, and I had this beautiful pop-star sister. So there was a time when I didn't feel great about myself. The song is about coming to the point where I'm like, Okay, I love who I am, and I'm happy being this person.

C: How did your singing career get off the ground?

A: While I was on 7th Heaven, I wrote music in my trailer, and I would go to the [recording] studio at night. Then finally my dad was like, "Okay, I'm taking you to record labels." There were definitely labels that turned me down because I wanted to do an indie kind of thing.

C: And then how did your reality show come about?

A: My dad said, "It's going to be good for you because people need to see your personality and see that you're not the same person as Jessica. They need to see how you make your record and that you're doing it yourself."

C: What's the hardest part of having your life taped 24-7?

A: When I was talking to a new guy and I didn't want my ex-boyfriend to see.

C Was there something you wish had been cut out?

A The ex-boyfriend thing…Josh [Henderson]. I'm glad they showed it, because a lot of my album is about him, but it just sucks that everyone knows what went on. He called me after it was on and was like "Thanks a lot."

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C: Are you friends with Josh?

A: Yeah. I'm one of those girls who can get hurt and then come back and be like "I can be your friend." Why dwell on something and hate somebody?

C: Do you think the show misrepresented you in any way?

A: It showed me very close to who I am. I have a few different sides. I'm goofy, but at the same time, I'm tough, and at the same time, I'm sensitive and nice.

C: The first season was about making your album. What's the new season about?

A: I'm headlining my first tour, so you're going to see that, and then you see that I just bought my new house. Everyone will expect that I'm gonna be the biggest mess. But this time, I have maids, so I'm not dealing with the dirt.

C: Describe your reaction when you found out your album hit number one.

A: It was so amazing. I had no clue that it would do that well on the charts. When my dad called me and said, "Your album's gone number one!" I was like, "Are you serious? Is this a joke?" And then I saw it on paper, and I started screaming. My dad sent me and my friends to Cabo [San Lucas,
Mexico] to celebrate.

C: "Pieces of Me" is about your most recent love, Ryan Cabrera, right?

A: Yeah. Ryan's my best friend, and before we started dating, we were best friends. When I was doing the album, I'd come home really frustrated and call Ryan, and he'd always make me feel so much better. So I wrote that song about him…a best friend that evolves into a love interest. Now we're kind of on-off, on-off. We still go on dates and do all that stuff. We just don't get to see each other that much. But when we're both home, we go out all the time. And we're actually about to go on tour together.

C: Is it weird that your dad is Ryan's manager?

A: It's good—when Ryan and I are off, I know what he's doing. I can find out if he's with another girl from my dad.

C: Did you dye your hair brown to differentiate yourself from Jessica?

A: No, I did it the day that I finished 7th Heaven. I wasn't going back to the show and I was sick of my hair, so I went to Target and bought a Clairol box and dyed it myself. I still dye my own hair.

C: In what ways are you and Jessica really different?

A: I will walk up to somebody and be like, "I don't like what you said to me," and she's more the shy type. I will walk up to anybody and confront anything, and she's more guarded.

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C: How are you the same?

A: We think it's important to be yourself. We're both goofy, and we like to laugh and be silly, and our hearts are similar. We might get a lot of things [given to us], but we like to give and make other people happy. And we both like shopping. As for music, we both like Maroon 5 and Norah Jones.

C: Is there any jealousy between the two of you?

A: I'm not jealous of her nor am I in competition with her. I'm proud of her, and I think that she's proud of me because she knows I've finally done what I wanted to do. And it took me a while to get there. My music is nothing like hers, so there's no competition there.

C: Do you believe in saving sex for marriage like Jessica?

A: I think that having sex before you're married is something that you should decide on your own. I never chose to speak up about it because it's something that if you're ready for, you should do, but if you're not ready, then you shouldn't do it.

C: What's a deal breaker for you with guys?

A: I can't stand it when guys talk about themselves. And I have to have someone who knows how to treat a woman. If a guy takes you out to dinner on your first date and doesn't pay…run!

C: What do you do for fun?

A: I go dancing with my girlfriends or go bowling. I love painting and making lamps. I love to knit…it takes your mind off of everything.

C: Is there something people don't know about you?

A: I'm really quite girlie. A lot of people see my tomboy side. But I need to get my manicures, and I need to get my facials. People think because I sing rock music that I don't really care that much about all that kind of stuff, but I do.

C: You have a new movie coming out called Wannabe….

A: Yeah, the movie's all about music. I play an actress who's a tomboy type of girl, and music saves her from all the things that she deals with in her life. I love acting, and I'm excited to do this movie, but singing is my focus.

C: Describe what it's like being on the cover of Cosmo.

A: I love Cosmo. Every month I get it. It's where I learn my little tricks.

C: What's the most fearless thing you've ever done? A: Putting my album out and being so open…and doing my reality show. I think that was probably the biggest step. Just going, "Here I am and here's my music and there you go…I hope you like it." I had to be fearless to do that.